Sr. Red Team Specialist

Cboe Global Markets; Chicago (IL); On-site; USD 121,550 - 157,300; Full time

Benefits offered by this job

Generous paid time off

Health, dental, and vision benefits

2:1 401(k) match

Paid Tuition assistance

Complimentary lunch and snacks

Job summary

Cboe Global Markets is seeking a Senior Red Team Specialist in Chicago, IL. This technical role focuses on executing advanced offensive security operations while collaborating closely with various security teams. Candidates should have a strong background in red teaming and penetration testing, coupled with excellent communication skills. The position offers a competitive salary range of $121,550 to $157,300, comprehensive benefits, and opportunities for professional development.

Qualifications

• 5+ years of experience in red teaming, penetration testing, or offensive security.
• Strong knowledge of attacker tradecraft and TTPs across enterprise environments.
• Hands‑on experience with endpoint, identity, cloud, and hybrid infrastructures.

Responsibilities

• Executing adversary emulation and red team engagements.
• Developing and maintaining custom red team tooling.
• Producing actionable reporting from findings.

Skills

Red teaming

Penetration testing

Offensive security

Technical documentation

Communication skills

Education

Bachelor’s degree or equivalent experience

Tools

Python

PowerShell

Bash

Job description

Role Overview

The Security Operations team is hiring a Senior Red Team Specialist. The Senior Red Team Specialist is a highly skilled individual contributor responsible for planning and executing advanced offensive security operations that emulate real‑world adversaries and rigorously test enterprise security controls. This role is deeply technical and hands‑on, with active engagement across endpoint, identity, cloud, SaaS, network, and application environments.

This position partners closely with Detection Engineering, Threat Hunting, Incident Response, and Purple Team functions to ensure red team engagements drive measurable improvements in detection coverage, response effectiveness, and overall defensive posture. While the role does not own enterprise‑wide red team strategy, it plays a key role in shaping red team tactics, tooling, and execution standards, and in translating offensive findings into actionable defensive outcomes.

Responsibilities

• Executing adversary emulation and red team engagements aligned to real‑world threat actor techniques and objectives
• Performing hands‑on offensive operations, including initial access, persistence, privilege escalation, lateral movement, and command‑and‑control
• Developing, maintaining, and safely using custom red team tooling, scripts, and techniques
• Working closely with detection and threat hunting teams to validate detections and response effectiveness during red and purple team exercises
• Assisting in the design and execution of assumed breach scenarios and multi‑stage attack chains
• Identifying control gaps, detection blind spots, and architectural weaknesses across enterprise environments
• Supporting incident response teams during complex investigations by providing attacker tradecraft insight
• Producing clear, actionable reporting that translates technical findings into operationally relevant recommendations
• Contributing to the improvement of red team processes, safety controls, and engagement playbooks
• Mentoring junior analysts and contributing to skills development across the security operations team

Qualifications

• 5+ years of experience in red teaming, penetration testing, or offensive security, with demonstrated hands‑on impact
• Bachelor’s degree or equivalent practical experience
• Strong knowledge of attacker tradecraft and TTPs across modern enterprise environments
• Hands‑on experience attacking and evading controls in endpoint, identity, cloud, and hybrid infrastructures
• Working understanding of defensive security technologies, such as EDR, SIEM, identity protection, and cloud security controls
• Experience collaborating in purple team exercises and adapting techniques based on detection feedback
• Ability to independently plan and execute offensive tasks within a defined engagement scope
• Strong written and verbal communication skills, including technical documentation and reporting
• High ethical standards and experience operating within defined rules of engagement

Preferred Experience

• Experience executing threat‑intelligence‑informed adversary emulation, not just vulnerability‑driven testing
• A track record of helping convert red team findings into improved detections or response playbooks
• Strong scripting or automation skills (e.g., Python, PowerShell, Bash) to support tooling and operations
• Familiarity with MITRE ATT&CK for mapping activity and communicating impact
• Experience operating in regulated or large enterprise environments
• Demonstrated ability to mentor junior analysts or contribute to internal training materials
• Curiosity, adaptability, and a continuous improvement mindset

Benefits and Perks

• Fair and competitive salary and incentive compensation packages with upside for overachievement
• Generous paid time off, including vacation, personal days, sick days and annual community service days
• Health, dental and vision benefits, including access to telemedicine and mental health services
• 2:1 401(k) match, up to 8% match immediately upon hire
• Discounted Employee Stock Purchase Plan
• Tax Savings Accounts for health, dependent and transportation
• Employee referral bonus program
• Volunteer opportunities to help you give back to your communities
• Complimentary lunch, snacks and coffee in any Cboe office
• Paid Tuition assistance and education opportunities
• Generous charitable giving company match
• Paid parental leave and fertility benefits
• On‑site gyms and discounts to other fitness centers
• Paid Time Off

Equal Employment Opportunity

We’re proud to be an equal opportunity employer that does not discriminate against any employee or applicant for employment based on any legally protected characteristic, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, or veteran status. We are committed to fostering a workplace where all individuals are valued and respected.

Visa Sponsorship

This position is not eligible for visa sponsorship. Candidates must be legally authorized to work in the United States without the need for employer sponsorship now or in the future.

Salary Range

At Cboe, we are committed to providing a competitive, transparent, and market‑informed total rewards program. The anticipated base salary range for this role is $121,550–$157,300, with actual compensation determined by job‑related factors such as skills, relevant experience, education, internal alignment, and location. This role may also be eligible for annual incentive compensation and, where applicable, participation in Cboe's long‑term equity programs.

Additional information about Cboe's total rewards program, including benefits and other compensation components, can be found at Total Rewards at CBOE.

Any communication from Cboe regarding this position will only come from a Cboe recruiter who has a @cboe.com email or via LinkedIn Recruiter. Cboe does not use any other third‑party communication tools for recruiting purposes.